Three Perfect Days in Key West — Country Nights & City Lights

I feel like most people either love Key West or hate it, I happen to be one that loves it. I love the live music at every turn, the fact that hippies and billionaires eat at the same restaurants, the general attitude of not caring, relaxation and fun is everywhere. I think this is what makes the tiny island so unique.

I stayed at the newly remodeled boutique hotel, Havana Cabana, and it was out of this world. I have stayed at a lot of properties on Key West, and this one might be my favorite. It has Key West's largest pool, live music in the evenings, many great places for photos, a Cuban food truck, and scooters, and bikes you can rent to explore the island.

Day 1

Check into your hotel, get settled, and head over to Blue Heaven for some of the most amazing breakfast you will ever have. It is known for its quirky decor, live music, fantastic food, and chickens that roam around while you eat. I recommend the Bloody Mary, Lobster Benedict, and you can't leave without the Key Lime Pie. I know it is breakfast, but you are on vacation! Work of that breakfast by grabbing the bikes and exploring the island. I find biking the most relaxed way to explore Key West since it is little and compact. You can bike it without getting tired and you can stop wherever you want. I recommend lunch at Schooners Wharf, the Mahi Mahi blackened is to die for, and most days, you get to listen to the songs and tales of Michael McCloud, who has played at this Bar longer than most of us have been alive. Ask him about Toby Keith if you want to hear a good story. After lunch, get back on the bikes for a stop at the Half Shell Raw Bar. This restaurant was featured on the Travel Channel and the cover of Kenny Chesney's “When I See This Bar”. Now it should be almost sunset, so time to head to Mallory Square for the sunset celebration. Grab a drink, watch a beautiful sunset and toast another perfect day in paradise. After that, I would find out if Zack Seemiller is playing and where, and go see him for a few hours. He always makes me laugh till I cry and is a Key West staple. He puts where he is playing every day on his Instagram @seemillerzack.

For DInner, I would make reservations beforehand at Latitudes and take a little ferry ride across to Sunset Key. Ask to sit outside and prepare to be blown away by this meal. The ambiance, food, and service are perfection. It is more on the dressy and pricy side.

Day 2

Wake up, grab a chair and soak up some of that sweet sunshine at the hotel pool. If you want breakfast, head down to Duval and check out the Banana Cafe for some melt in your mouth crepes. While you are there, check out the local art shops. The talent in Key West is fantastic, from local photographers to artists, to pottery, you will surely find a great souvenir.

Around lunch, go to the DJ's Crab Shack, featured in Diners, Drive-In, and Dives for some clams or a delicious lobster roll. Then you can stop for a margarita at the original Margaritaville restaurant created by Jimmy Buffett. It is small, but you never know who will pop in to play. When you are wasted away again at Margaritaville and ready for a change, you can make your way to the other famous bars on Duval, Sloppy Joes, which has been around since 1933, and Hogs Breath, where Kenny Chesney did a concert a few years back. You can also stop by Ernest Hemingway's estate and do a tour. Must like cats because there are still around 40 of them roaming the property.

Have dinner and watch sunset at the Perry Hotel, which is a little off the island but has a delicious restaurant (Matt’s Stock Island Kitchen and Bar) and even better views of the Marina that hosts yachts to fishing boats. Get your google ready to find out how much these yachts are worth and who they belong too. If you make a reservation beforehand, ask to sit outside.

Day 3

Rent a boat and go exploring or take a guide and go deep-sea fishing. If you are in for a more relaxing day, find one of the best kept secret beaches, located right behind Lagerheads beach bar on 0 Simonton Street. There is also a bigger public beach called Smathers, which is on the east side of the island.

In the evening head to Ambrosia which is a sushi restaurant that I never miss while in Key West. Don't get too full, though, because dessert is at the infamous Better than Sex. Take a look at their specialty dessert cocktails and wine. The names of the drinks will make you laugh, but the place will leave you wanting more.

Before you leave Key West, if you are feeling brave, head up the stairs on the left of the Bull Bar, and you will soon find yourself in the Garden of Eden. You are now in a rooftop clothing-optional Bar. You do not have to get naked or body painted (though it is an option). You can't, however, touch your cell phone. Enjoy the craziness that you only see in Key West.